More than a thousand people make the daily commute from the Wairarapa to Wellington, and they do it by going through a mountain. The 8.8-kilometre Rimutaka rail tunnel, opened in November 1955, turned the Wairarapa from a place separated by the ranges into a place connected by them. Before the tunnel, trains climbed the Rimutaka Incline using a Fell centre-rail system that required up to five locomotives and topped out at 8 km/h. The Wairarapa Connection now runs five services each way on weekdays and two on weekends, stopping at Featherston, Woodside, Matarawa, Carterton, and three stations in Masterton. Evening peak services fill to standing room during school holidays. Cyclists have their own route over the ranges via the Remutaka Rail Trail, which follows the old incline formation through native bush. The trail is largely gentle on the Hutt Valley side but steeper and more gravelly on the Wairarapa descent, where a mountain bike becomes a necessity.

The Wairarapa's wine region is small compared to Marlborough and Hawke's Bay, but what it lacks in scale it makes up in reputation. Martinborough is the heart of it, a grid of streets laid out around a central square where cellar doors outnumber other businesses. Pinot Noir is the flagship grape, and Wairarapa's examples routinely place in national and international competitions. Sauvignon Blanc is the other major variety, but the region also produces aromatic wines, Pinot Gris and Riesling among them, that benefit from the warm days and cool nights the sheltering ranges provide. Smaller growing areas at Gladstone, east of Carterton, and north of Masterton extend the vineyard map, though Martinborough remains the name most visitors know. The wine industry has brought with it restaurants, boutique accommodation, and a weekend tourism economy that complements the farming base the valley has relied on for generations.

Masterton is the largest town and the commercial center. Carterton, a short drive from tramping tracks in the Tararua Ranges, offers river swimming and access to the backcountry. Greytown, with its heritage timber buildings, is the kind of place where the main street rewards a slow walk. Featherston sits at the southern gateway, where State Highway 2 begins its narrow, winding 15-kilometre climb over the Rimutaka Range, one of the country's worst crash blackspots. Beyond the main towns, the Wairarapa stretches east to Castlepoint on the rugged coast, where a lighthouse stands above reef-carved formations. The region's terrain is mostly flat, making cycling practical for short distances, though a car opens up the full landscape. Bus services link the main centres with each other and with train connections, though they do not run on Sundays or public holidays.

The Wairarapa's character comes partly from its geography. The ranges that shelter it also separate it, creating a sense of remove that feels larger than the actual distance from Wellington. There have been no air services to the region since February 2014, which means the train and the road are it. State Highway 2 provides the northern connection through to Hawke's Bay, while the Pahiatua Track, a sealed road despite its name, links to Palmerston North through quieter country. The relative isolation has preserved something. The pace of the Wairarapa is unhurried. The sheep and dairy farms that make up the working landscape have not been replaced by suburbs. The hospital in Masterton handles the region's emergencies. The vineyards draw visitors but have not overwhelmed the towns. Wellington is close enough for a daily commute but far enough, on the other side of a mountain range, to feel like somewhere else entirely.